Record Information
Version1.0
Creation date2010-04-08 22:12:57 UTC
Update date2019-11-26 03:14:27 UTC
Primary IDFDB017211
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvin
DescriptionMalvin, also known as malvoside, belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Malvin is an extremely weak basic (essentially neutral) compound (based on its pKa). Malvin is found, on average, in the highest concentration within nectarines. Malvin has also been detected, but not quantified in, several different foods, such as common beans, green beans, yellow wax beans, grapes, and highbush blueberries. This could make malvin a potential biomarker for the consumption of these foods.
CAS Number16727-30-3
Structure
Thumb
Synonyms
SynonymSource
Malvidin-3,5-diglucosideHMDB
MalvosideHMDB
Malvidin 3,5-diglucosideHMDB
MalvinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP-0.01ALOGPS
logP-2.5ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area270.82 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity159.35 m³·mol⁻¹ChemAxon
Polarizability62.75 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC29H35O17
IUPAC name7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,5-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C29H34O17/c1-40-15-3-10(4-16(41-2)20(15)33)27-17(44-29-26(39)24(37)22(35)19(9-31)46-29)7-12-13(42-27)5-11(32)6-14(12)43-28-25(38)23(36)21(34)18(8-30)45-28/h3-7,18-19,21-26,28-31,34-39H,8-9H2,1-2H3,(H-,32,33)/p+1
InChI KeyCILLXFBAACIQNS-UHFFFAOYSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=C(OC2OC(CO)C(O)C(O)C2O)C=C2C(OC3OC(CO)C(O)C(O)C3O)=CC(O)=CC2=[O+]1
Average Molecular Weight655.578
Monoisotopic Molecular Weight655.187424694
Classification
Description belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-5-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.13%; H 5.38%; O 41.49%DFC
Melting PointMp 165 dec. (chloride)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rl-5200198000-afe143af9ae9c60ab0f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0100009000-aec227f7d12e2bcd670eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1200009000-2030b1af6672f5d99bd9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900021000-bb0a26a9a11c4e7fe9e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1200009000-3f53e3441e078a393c67JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-5500009000-0280f0b8365ee7e3f777JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100110000-efd56933b2b74f600083JSpectraViewer
ChemSpider ID3056859
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3830888
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID20
DrugBank IDNot Available
HMDB IDHMDB38009
CRC / DFC (Dictionary of Food Compounds) IDCNF63-A:KWN86-S
EAFUS IDNot Available
Dr. Duke IDMALVIN
BIGG IDNot Available
KNApSAcK IDC00002384
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMalvin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.